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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:03:41 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033345

Secondary Accession Numbers

HMDB33345

Metabolite Identification

Common Name

(±)-Ribaline

Description

(±)-Ribaline belongs to the class of organic compounds known as dihydrofuranoquinolines. These are organic heterocyclic compounds with a structure based on the dihydrofuranoquinoline skeleton (±)-Ribaline has been detected, but not quantified in, herbs and spices. This could make (±)-ribaline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-Ribaline.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033345
     RDKit          3D
(±)-Ribaline
 37 39  0  0  0  0  0  0  0  0999 V2000
    0.9721    1.0142   -2.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783    0.3920   -1.2010 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047    0.1742   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.4108    0.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3106   -0.7876    1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -1.3191    2.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332   -0.5549    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945   -0.9262    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935   -0.6936    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743   -1.0561    0.6529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -0.1050   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906    0.2633   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809    0.0323   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -0.5106    1.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -0.3065    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4280    0.4570    0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    0.7383   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2622   -0.3339    1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591    1.6449    1.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341    0.4430   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    0.2492   -3.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6015    1.9255   -2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0762    1.3595   -2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -1.3809    1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -0.3168    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5033    0.0710   -1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    0.7231   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639   -1.4825    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296    0.2735    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526   -1.2643   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7674   -0.1772   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0289    1.4850   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701    1.1318   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9881   -0.1385    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3380   -0.0551    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1334   -1.4282    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.8809    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  1  0
 13  2  1  0
 20  3  1  0
 13  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv0541 02241210272D          

 20 22  0  0  0  0            999 V2000
   -0.3709   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1134   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1134    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    0.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1134   -0.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6085   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585   -0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160   -0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1134    0.6593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 16  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 17  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 20  1  0  0  0  0
  9 10  2  0  0  0  0
  9 19  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033345

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(CC(O2)C(C)(C)O)C(=O)C2=C1C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H17NO4/c1-15(2,19)12-7-10-13(18)9-6-8(17)4-5-11(9)16(3)14(10)20-12/h4-6,12,17,19H,7H2,1-3H3

> <INCHI_KEY>
ONPUKGULNMQBLF-UHFFFAOYSA-N

> <FORMULA>
C15H17NO4

> <MOLECULAR_WEIGHT>
275.2998

> <EXACT_MASS>
275.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.154135782793276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-2-(2-hydroxypropan-2-yl)-9-methyl-2H,3H,4H,9H-furo[2,3-b]quinolin-4-one

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.719940342666667

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.294365620443525

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.733234212528322

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1074496961947355

> <JCHEM_POLAR_SURFACE_AREA>
70.00000000000001

> <JCHEM_REFRACTIVITY>
84.9091

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-2-(2-hydroxypropan-2-yl)-9-methyl-2H,3H-furo[2,3-b]quinolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033345
     RDKit          3D
(±)-Ribaline
 37 39  0  0  0  0  0  0  0  0999 V2000
    0.9721    1.0142   -2.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783    0.3920   -1.2010 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047    0.1742   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.4108    0.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3106   -0.7876    1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -1.3191    2.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332   -0.5549    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945   -0.9262    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935   -0.6936    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743   -1.0561    0.6529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -0.1050   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906    0.2633   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809    0.0323   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -0.5106    1.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -0.3065    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4280    0.4570    0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    0.7383   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2622   -0.3339    1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591    1.6449    1.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341    0.4430   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    0.2492   -3.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6015    1.9255   -2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0762    1.3595   -2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -1.3809    1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -0.3168    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5033    0.0710   -1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    0.7231   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639   -1.4825    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296    0.2735    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526   -1.2643   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7674   -0.1772   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0289    1.4850   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701    1.1318   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9881   -0.1385    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3380   -0.0551    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1334   -1.4282    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.8809    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  1  0
 13  2  1  0
 20  3  1  0
 13  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.692  -1.539   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.078  -0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.464  -1.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.697  -0.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.697   0.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.464   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.078   0.769   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.692   1.539   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.538   0.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.538  -0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.078  -1.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.003  -0.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.543  -0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.083  -0.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.697   1.539   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.692  -3.079   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.083  -1.539   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.697  -1.539   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.078   1.231   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.692   3.079   0.000  0.00  0.00           C+0
CONECT    1    2   10   16                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   19                                                  
CONECT   10    1    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15   18                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    1                                                            
CONECT   17    4                                                            
CONECT   18   13                                                            
CONECT   19    9   12                                                       
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033345
HETATM    1  C1  UNL     1       0.972   1.014  -2.525  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.078   0.392  -1.201  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.005   0.174  -0.451  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.088  -0.411   0.798  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.311  -0.788   1.300  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.475  -1.319   2.412  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.433  -0.555   0.505  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.694  -0.926   0.986  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.794  -0.694   0.197  1.00  0.00           C  
HETATM   10  O2  UNL     1       6.074  -1.056   0.653  1.00  0.00           O  
HETATM   11  C8  UNL     1       4.630  -0.105  -1.039  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.391   0.263  -1.519  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.281   0.032  -0.731  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.287  -0.511   1.369  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.171  -0.306   0.156  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.428   0.457   0.522  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.226   0.738  -0.712  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.262  -0.334   1.489  1.00  0.00           C  
HETATM   19  O3  UNL     1      -3.059   1.645   1.188  1.00  0.00           O  
HETATM   20  O4  UNL     1      -1.334   0.443  -0.689  1.00  0.00           O  
HETATM   21  H1  UNL     1       1.231   0.249  -3.260  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.601   1.926  -2.581  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.076   1.360  -2.624  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.812  -1.381   1.943  1.00  0.00           H  
HETATM   25  H5  UNL     1       6.553  -0.317   1.177  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.503   0.071  -1.647  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.245   0.723  -2.480  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.464  -1.483   1.866  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.430   0.273   2.139  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.453  -1.264  -0.304  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.767  -0.177  -1.010  1.00  0.00           H  
HETATM   32  H12 UNL     1      -5.029   1.485  -0.444  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.570   1.132  -1.516  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.988  -0.139   2.544  1.00  0.00           H  
HETATM   35  H15 UNL     1      -5.338  -0.055   1.389  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.133  -1.428   1.281  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.154   1.881   0.819  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   13
CONECT    3    4    4   20
CONECT    4    5   14
CONECT    5    6    6    7
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   11   11
CONECT   10   25
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   14   15   28   29
CONECT   15   16   20   30
CONECT   16   17   18   19
CONECT   17   31   32   33
CONECT   18   34   35   36
CONECT   19   37
END

HMDB0033345
     RDKit          3D
(±)-Ribaline
 37 39  0  0  0  0  0  0  0  0999 V2000
    0.9721    1.0142   -2.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783    0.3920   -1.2010 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047    0.1742   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.4108    0.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3106   -0.7876    1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -1.3191    2.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332   -0.5549    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945   -0.9262    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935   -0.6936    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743   -1.0561    0.6529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -0.1050   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906    0.2633   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809    0.0323   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -0.5106    1.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -0.3065    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4280    0.4570    0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    0.7383   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2622   -0.3339    1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591    1.6449    1.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341    0.4430   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    0.2492   -3.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6015    1.9255   -2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0762    1.3595   -2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -1.3809    1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -0.3168    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5033    0.0710   -1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    0.7231   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639   -1.4825    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296    0.2735    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526   -1.2643   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7674   -0.1772   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0289    1.4850   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701    1.1318   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9881   -0.1385    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3380   -0.0551    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1334   -1.4282    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.8809    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  1  0
 13  2  1  0
 20  3  1  0
 13  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₇NO₄

Average Molecular Weight

275.2998

Monoisotopic Molecular Weight

275.115758037

IUPAC Name

6-hydroxy-2-(2-hydroxypropan-2-yl)-9-methyl-2H,3H,4H,9H-furo[2,3-b]quinolin-4-one

Traditional Name

6-hydroxy-2-(2-hydroxypropan-2-yl)-9-methyl-2H,3H-furo[2,3-b]quinolin-4-one

CAS Registry Number

41234-32-6

SMILES

CN1C2=C(CC(O2)C(C)(C)O)C(=O)C2=C1C=CC(O)=C2

InChI Identifier

InChI=1S/C15H17NO4/c1-15(2,19)12-7-10-13(18)9-6-8(17)4-5-11(9)16(3)14(10)20-12/h4-6,12,17,19H,7H2,1-3H3

InChI Key

ONPUKGULNMQBLF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrofuranoquinolines. These are organic heterocyclic compounds with a structure based on the dihydrofuranoquinoline skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Dihydrofuranoquinolines

Direct Parent

Dihydrofuranoquinolines

Alternative Parents

Substituents

Dihydrofuranoquinoline
Dihydroquinolone
Hydroxyquinoline
Dihydroquinoline
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Vinylogous ester
Vinylogous amide
Tertiary alcohol
Heteroaromatic compound
Azacycle
Ether
Oxacycle
Organic nitrogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033345)
Cytoplasm (HMDB: HMDB0033345)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033345)

Source

Exogenous

Food

Food (HMDB: HMDB0033345)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033345)

Not Available

Nutrient (HMDB: HMDB0033345)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	268 - 269 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.72	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.73	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.91 m³·mol⁻¹	ChemAxon
Polarizability	29.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.547	31661259
DarkChem	[M-H]-	161.604	31661259
DeepCCS	[M+H]+	164.339	30932474
DeepCCS	[M-H]-	161.981	30932474
DeepCCS	[M-2H]-	194.867	30932474
DeepCCS	[M+Na]+	170.432	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	166.2	32859911
AllCCS	[M+Na]+	167.2	32859911
AllCCS	[M-H]-	168.9	32859911
AllCCS	[M+Na-2H]-	168.6	32859911
AllCCS	[M+HCOO]-	168.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Ribaline	CN1C2=C(CC(O2)C(C)(C)O)C(=O)C2=C1C=CC(O)=C2	3147.4	Standard polar	33892256
(??)-Ribaline	CN1C2=C(CC(O2)C(C)(C)O)C(=O)C2=C1C=CC(O)=C2	2502.3	Standard non polar	33892256
(??)-Ribaline	CN1C2=C(CC(O2)C(C)(C)O)C(=O)C2=C1C=CC(O)=C2	2815.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-Ribaline,1TMS,isomer #1	CN1C2=C(CC(C(C)(C)O[Si](C)(C)C)O2)C(=O)C2=CC(O)=CC=C21	2497.0	Semi standard non polar	33892256
(??)-Ribaline,1TMS,isomer #2	CN1C2=C(CC(C(C)(C)O)O2)C(=O)C2=CC(O[Si](C)(C)C)=CC=C21	2565.8	Semi standard non polar	33892256
(??)-Ribaline,2TMS,isomer #1	CN1C2=C(CC(C(C)(C)O[Si](C)(C)C)O2)C(=O)C2=CC(O[Si](C)(C)C)=CC=C21	2604.3	Semi standard non polar	33892256
(??)-Ribaline,1TBDMS,isomer #1	CN1C2=C(CC(C(C)(C)O[Si](C)(C)C(C)(C)C)O2)C(=O)C2=CC(O)=CC=C21	2741.0	Semi standard non polar	33892256
(??)-Ribaline,1TBDMS,isomer #2	CN1C2=C(CC(C(C)(C)O)O2)C(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	2784.6	Semi standard non polar	33892256
(??)-Ribaline,2TBDMS,isomer #1	CN1C2=C(CC(C(C)(C)O[Si](C)(C)C(C)(C)C)O2)C(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3055.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Ribaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9560000000-aa364e2e734a762da673	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Ribaline GC-MS (2 TMS) - 70eV, Positive	splash10-0flc-9424300000-b8da907e26b24908a092	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Ribaline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 10V, Positive-QTOF	splash10-056r-0090000000-54d01f7f29f9be75201c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 20V, Positive-QTOF	splash10-0a6r-1090000000-bf8b77d0d4626ba5af65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 40V, Positive-QTOF	splash10-00u6-3390000000-b113def5727474969ac1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 10V, Negative-QTOF	splash10-00di-0090000000-bee2b1527a043901a1ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 20V, Negative-QTOF	splash10-05fr-0090000000-9e9d1b42ea95dd852313	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 40V, Negative-QTOF	splash10-052f-1390000000-005a39aa1625ffd2cf64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 10V, Positive-QTOF	splash10-004i-0090000000-f39a3970d85a983b3272	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 20V, Positive-QTOF	splash10-004i-0290000000-1a6c54ba54367c33e199	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 40V, Positive-QTOF	splash10-006t-5940000000-0aab757b52fe654ce168	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 10V, Negative-QTOF	splash10-00di-0090000000-f84264cd76223545b055	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 20V, Negative-QTOF	splash10-00di-1090000000-cabfc20680333f3139aa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Ribaline 40V, Negative-QTOF	splash10-0006-3590000000-806c13b92deecde92bea	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011373

KNApSAcK ID

Not Available

Chemspider ID

298076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

336321

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-Ribaline (HMDB0033345)

MOL for HMDB0033345 ((±)-Ribaline)

3D MOL for HMDB0033345 ((±)-Ribaline)

3D SDF for HMDB0033345 ((±)-Ribaline)

3D-SDF for HMDB0033345 ((±)-Ribaline)

PDB for HMDB0033345 ((±)-Ribaline)

3D PDB for HMDB0033345 ((±)-Ribaline)

SMILES for HMDB0033345 ((±)-Ribaline)

INCHI for HMDB0033345 ((±)-Ribaline)

Structure for HMDB0033345 ((±)-Ribaline)

3D Structure for HMDB0033345 ((±)-Ribaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra